What’s your gender? Man
How old are you? 54
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Michigan
Highest education received: Some college (not currently in college)
What’s your occupation? Executive
What’s your current relationship status? Engaged/Married (monogamous)
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Adventurous. Experienced.
How many sexual partners have you had in your life (including oral sex)? 350+
How many hookup stories have you here posted before? 2
The Neighboring Nurse
How long ago did this hookup happen? 1979
What was your relationship status at the time? Single
How would you best classify this hookup? Just the beginning
How long did you know the person before this hookup? For more than 3 years
Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? J. lived across the street from us. She was 36 years old, twice my age at the time of our first hookup. J. was short, about 5 feet tall; weighed about 110 lbs.; had dark, naturally wavy, top-of-the-shoulder length hair; brown eyes; on the heavy side of B-cup breasts; smoked about 3 packs of cigarettes and drank about 2 pots of coffee nearly every day. She was a registered nurse at one of the local hospitals and worked the night shift, so mostly people in the neighborhood usually only saw her in her nurse’s whites.
J. grew up in the same neighborhood, at the other end of the street from where we lived at the time. She was a very kind woman, always looking out for her friends and neighbors, but was a single mother of two sons and was never married. She was somewhat notorious in the neighborhood for having had sex on the couch, which was in front of the picture window facing the street in her parents’ home, with the drapes open, making her very visible to passersby; so she was known in the subdivision as a slut/whore, and most boys simply fantasized about her from afar as we were instructed to steer clear of “women like that.” I had talked with her a number of times over the last several years, being her regular lawn mowing guy, however, and being very sexually active since my early teens and developing a bolder demeanor when it came to girls/women. But I never had the guts to come on to her (even though I always wanted to get into her) because she was so much older than I.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was starting my senior year in high school when J. asked if I would consider regularly sitting her two sons overnight while she went to work. I told her I would have to get permission from my parents, seeing that I was still a minor at that time (17, just a month before my birthday) and still living at home while going to high school. Having received permission from my parents to sit for her, I made arrangements to start a couple days after the beginning of the school year, making $9 per night (which was pretty good because I didn’t have any bills other than gas and insurance for my car and I could sleep in her bed and drink her coffee and milk, and eat nearly anything I wanted while there; and I had a regular job in the evenings where I made most of my money).
I would be out of bed and dressed when J. came home in the mornings, and we would talk for a few minutes before I went home to get ready for school. The talks became longer and more personal, which made it so that I had to be in a bit more of a rush to get to school on time, so my mother would “encourage” me to get home sooner (i.e., not spend so much time at J.’s in the mornings) so that I could be to school with a bit more of a time cushion. So, for about a week I would get home shortly after J. got home from work, but our conversations were warming up some more, even though they were necessarily shorter for a while.
One Saturday morning in October, J. got home a little bit early so that she could go to breakfast with her sister. Being a weekend I was able to stay over with her boys while she went out. When they came back she introduced me to her sister, who was a couple years older than J., very pretty herself, and who gave me a slightly longer than normal once-over, which was pretty encouraging for an 18 year old very sexually active guy. Then she looked at J. and said with a smirk, “Have a really nice morning.”
Her sister left, and J. and I sat at the kitchen table chatting about whatnot, and starting to flirt a little bit. After about 20 minutes she got up and said she would be right back, then went to her bedroom and changed out of her nursing uniform into some loose slacks and a tight t-shirt that outlined her very perky nipples. I had a flash thought of grabbing her tits as she walked by but was still a little too scared to be quite that bold. After pouring us each a warm up coffee she went into the other room and came right back, but this time she lightly brushed her breasts up against my left shoulder as she past me. I knew it was no accident because there was plenty of room for her to get by without turning sideways. I commented that she was very warm, to which she said there was something she wondered about. I asked her, “What’s that?” Instead of answering with words she came over and kissed me before sitting down again on the other side of the table. Of course, I kissed her back but surprised her with some tongue. She said, “We had better be careful.” And that was the beginning of some very open flirting on both our parts.
After that, when she got home in the mornings we would make out for a few minutes before I left, which pretty quickly led to rubbing each others ass, and after about another week or so I escalated it by starting to pull her top out of her slacks and wrapping my arms around her under her top, then a couple days later I went right for her breasts, opening her top and letting them loose so that I could get my mouth on them. This made her moan almost instantly, but then she tried to slow it down by telling me to not suck on them. This went on nearly every morning for about two weeks – kissing, rubbing and squeezing each others ass, fondling her breasts. Finally I decided that I wanted her to touch me too, so when she came home one Saturday morning I acted as if I were still sleeping in her bed. She came in, sat down next to me then bent over and kissed me good morning. As I “woke up”, I pulled her down on top of me and took her hand and placed it on my stomach, which was pretty chiseled, as I was athletic and did several hundred sit-ups every morning before taking my shower. She rubbed my tummy for a moment before I nudged her hand downward. She hesitantly went down to my crotch to find a raging hard-on, to which she let out a slight gasp and withdrew her hand after only a moment, saying that we couldn’t do that. I asked why and she told me that she was too old for me. I asked her with a little snicker in my voice, “All your parts still work, right?” To which she replied softly, “Please go home now. Let me think about this for a while. I have a long weekend and don’t go back in until Tuesday night. I need time to think about things. I’ll see you Tuesday night.”
What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? When I got to J.’s place Tuesday evening she was already to bolt out the door saying that she had to get to work a few minutes early for a meeting, and that she had an appointment the next morning. I really didn’t have a chance to say anything to her before she left, almost slamming the door behind her.
The next morning when J. came home, I already had my coat on and was ready to walk out when she said, “Take your coat off. We need to talk for a few minutes. I’ll get the cups.” I always had her coffee made for her when she got home.
We sat down at the kitchen table and she started talking. She said something along the lines of, “You know I already have a boyfriend, and if he ever found out that we even kissed that he would kill the both of us; he always carries a gun and has used it before.”
I told her that I wasn’t scared of Chuck because I had talked with him many times, and even worked on some of his cars and his boat with him a number of times over the past few years. Besides, I assured her that I could keep a secret. We discussed a few different things before I said that I had to get going. I got up from the table, gave her a kiss on her cheek, then grabbed my coat and was on my way to the door when she spoke up and said, “If you stay I’ll sleep with you.” Well, I turned around and told her, “I think you’re teasing me.” And I turned and started walking toward the door again with one arm in a coat sleeve when I heard her chair slide quickly as she got up and quick-stepped over to me and grabbed my arm, turned me around and said, “I want to sleep with you, now.” And then she stood on her tiptoes to kiss me. We kissed for just a moment before I picked her up and carried her into her bedroom, and laid her down on the bed. It seemed we couldn’t strip each other fast enough. As soon as I got her top open I grabbed her slacks and pulled them off from the bottom hems with one quick tug. I then dropped between her legs and started eating her out, to which she was shocked because, as she said later, she had never even heard about anybody doing that. She had three or four orgasms in quick succession, probably within the first 5 – 8 minutes. After eating her to several orgasms I climbed on top of her and slid inside in the missionary position, which is where we stayed for that entire first time fuck, except for when I got on my knees and held her legs up and apart while drilling her hard. She had several more orgasms before I shot my load deep inside her pussy after about 20 minutes or so of heavy duty fucking action, and then kept on pumping until I shot another load within just about 5 more minutes.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, more than one
Did your partner have an orgasm? Yes, multiple
What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? After my second shot of cum in her pussy, I rolled off her and we held each other and made out for a few minutes until the phone rang. It was my mother telling me I was late and asking if I was going to get to school. We talked as I got dressed, telling each other how enjoyable it was and how we both wished we had started sex sooner. We agreed to keep it as our secret but that we would most definitely get together at least a couple times each week. (J. had had a complete hysterectomy a couple of years earlier so she never had periods anymore, which made for a whole lot of sex, nearly any time I wanted it.)
I liked J. as both a friend and as a new fuck-buddy/FWB (although those terms were not in use yet at that time.) J. and I had sex several times every month until I went to college a few years later. And, after I recovered from a near fatal accident we started up again. We both initiated sex at different times and in different places over the years, and were great friends to boot. About 7 years after our first hookup J. moved out of town to take care of her mother, which ended our escapades. We both cried when she left.
There have been many times that I have thought of J. and our experiences together. Sometimes over the years I have wondered how she is doing. My mother said she saw her a few years ago and said that she looked rather rough, haggard even, and very unhealthy, as if she was trying to smoke herself to death. I felt sorry for J. and wished I could tell her that I appreciated her friendship and the times we had, for fuck’s sake and for lovemaking, and especially as good friends. I wish her all the best.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Hoping or expecting it would lead to something more, Thought it was an important experience to have, Didn’t want to disappoint my partner, I wanted to know if she would feel any different than the high school girls I was fucking.
How intoxicated were you? Not at all (no alcohol or drugs)
How intoxicated was your partner? Not at all (no alcohol or drugs)
How wanted was this hookup for you at the time? Very
Did you consent to this hookup at the time? I gave enthusiastic consent
How wanted was this hookup for your partner at the time? Very
Did your partner(s) consent to this hookup? They gave enthusiastic consent
To whom did you talk about the hookup? How did they react? I only talked about being with J. with my best friend one time after she moved away. I told him how I would wake her up sometimes and tell her that I was going to have another guy come fuck her with me, and that she usually smiled at the idea, but that I kind of regretted not having him with me at least once. He punched me in my arm and told me that if I ever had another girl that was willing to have two guys at once again and didn’t get him in on the action that he was going to kick my ass. We laughed. He was real cool about it, and somewhat jealous.
How would you best summarize people’s reactions about this hookup? Relatively positive
Did you get emotionally hurt as a result of this hookup? Not at all
Did your partner get emotionally hurt as a result of this hookup? Not at all
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? I was 18, and she was 36 the first time we fucked, and it led to nearly 7 years of having a regular partner who didn’t care that I was fucking other women, as long as it wasn’t in her house. We even talked about some of my other lady friends a few times, and talked about getting into a threesome, both FMF and MFM, but it never happened.
What was the WORST thing about this hookup? I could have gone another round or two but I was already late for school.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Being that it was my first experience with a woman who was old enough to be my mother, I realized that I wasn’t locked into having sex just with girls my own age, and that older women were still active, and some were attracted to younger men.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
Anything else you want to add about this hookup? As I stated above, J. and I maintained a long, open relationship/friendship. I was the first person to introduce her to cunnilingus; later I was the first man whose cock she sucked; the first whose cum she swallowed, and also the first one to have anal sex with her. Maybe I’ll write about some of those firsts another time. But for now, it was worth being late for school and flunking a test in sociology class. I’d do it again if I could.
What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Casual sex has been a big part of my life since I was about 14 years old. I have enjoyed CS many thousands of times with several hundred partners, some as one night stands, some FWB or fuck-buddies, and even within committed relationships. CS can be a negative when it is either coerced or to try to improve ones self image/self respect. If one party is coerced, then that can be considered a form of rape both legally and morally. In order to safely enjoy casual sex one should not expect it to be a cure or a tool to improve ones self image or social standing, but instead it should be viewed as recreation and relaxation, as it can definitely fulfill both of those needs, but ONLY when all parties are willingly consenting.
I think that CS is practiced by more people than would admit it even in a completely anonymous survey. That being said, there are not as many who enjoy it regularly as many of us would like to imagine.
I would like to see the social stigma erased for both men and women who choose to enjoy casual sex, whether on a rather regular basis or simply as an occasional diversion.
What do you think about the Casual Sex Project? Great forum! I enjoy reading about others’ experiences.
You have a hookup story to share? Submit it here!Story Views: 4,197